Boston Red Sox: An Early Breakdown of Their Best Trade Bait

The Boston Red Sox knew repeating as World Series champions in 2014 wouldn’t be an easy task. Through their first 26 games, they're finding out how hard it actually will be.

Manager John Farrell has watched his team struggle to a 12-14 record, good for fourth place in the American League East.

MLB’s regular season is five months long for a reason—this is a marathon, not a sprint. A strong start to the year is helpful, but a slow one won’t doom a team to miss the postseason.

The next month or two is important for the fate of the 2014 Red Sox. We will soon find out whether they’re legitimate contenders or not. The route this team takes in the near future will also determine if any in-season trades happen.

If Boston ends up falling out of contention, which players should they look to deal? Let’s take a look at some early-season trade bait.

Jon Lester

General manager Ben Cherington hoped to lock up key players to contract extensions prior to the start of the 2014 season. He was successful in extending David Ortiz, but not so much with Jon Lester.

In the final season of a team-friendly six-year, $42.75 million contract, the southpaw is looking for a significant raise in the next deal he signs.

Negotiations were moving slowly all spring but are now tabled until the offseason. Ken Rosenthal of FOX Sports reported Boston “lowballed” Lester with a four-year offer worth approximately $70-80 million. The lefty is willing to take a hometown discount, but not by that much.

The Red Sox still have an exclusive negotiation period with Lester prior to free agency this winter. However, the offer probably must increase to around $100 million if they plan on retaining him.

After returning to form in 2013, Lester has continued his strong performance on the mound. Through six starts and 40.2 innings pitched, he owns a 2-4 record with a 3.10 ERA, 1.23 WHIP and 43 strikeouts.

This “lowball” offer may not be the reason Boston loses Lester to free agency. However, dangling him in potential trade talks to get a sense of his worth to other teams isn't a bad idea, especially if Cherington doesn't think an agreement will be reached.

A team in contention looking to bolster its rotation may be willing to give up impact prospects to land him, even if he doesn’t re-sign at the end of the year.

Of course, this should only be a serious consideration if Boston’s playoff hopes evaporate by the summer.

Jake Peavy

Michael Dwyer

The Red Sox made a bold move to acquire Jake Peavy from the Chicago White Sox last summer to fortify their rotation. Despite posting a 7.11 ERA in 12.2 postseason innings, he brought more veteran experience to the front of the pitching staff in 2013.

Peavy is in the final guaranteed year of his current contract—he can activate a player option depending on his performance and health—and is starting the year very well.

The veteran right-hander is 1-0 with a 2.87 ERA, 1.37 WHIP and 32 strikeouts through 31.1 innings of work. He’s also showed consistency, working into the sixth inning in each of his five starts.

Similar to 2013, Peavy could be an interesting trade target for teams in need of starting pitching. With the amount of hurlers heading for Tommy John surgery, there are plenty of teams perceived to have a need.

Again, Boston’s performance over the next month or two will dictate whether Cherington is comfortable exporting an effective piece of his rotation. If Clay Buchholz and Felix Doubront are more consistent, it would make a potential deal easier to fathom.

In Triple-A, Rubby De La Rosa and Allen Webster are off to good starts and should be considered candidates to replace Peavy if he's traded away. Brandon Workman currently owns a 6.28 ERA through his first three starts, but he can also be an option if a void in the rotation is created.

Grady Sizemore

Charles Rex Arbogast

A hot start in the season’s first two weeks has evaporated for Grady Sizemore, who is now hitting .208/.275/.361 with two home runs and seven RBI in 72 at-bats.

If he stays healthy, there is a good chance he will get back into a groove at the plate. His previous track record alone will probably have some teams interested in him as a fourth outfielder or bat off the bench.

The return of Shane Victorino from the disabled list on April 23 gives Farrell some more flexibility with his outfield. Despite hitting .230/.337/.338 in 74 at-bats, Jackie Bradley Jr. has shown the ability to contribute at the big league level.

Bradley is still viewed as the long-term solution in center field. Farrell has not been afraid to keep JBJ in the lineup as the leadoff hitter because he's been his best option to put there.

If Victorino produces like he did in 2013 and Daniel Nava finds his swing in Triple-A, Sizemore could become available, especially if Bradley is trusted to play every day.

What Boston could get in return for Sizemore depends on his production as the season progresses. If April is any indication, he will get plenty of opportunities to make an impact, prove his durability and build his trade value.

Chris Capuano

Kathy Willens

Chris Capuano’s performance to start the season has been impressive. Through his first 14.1 innings pitched, he hasn’t allowed a run while owning a 0.70 WHIP with 15 strikeouts.

Unlike Lester and Peavy, it would be more conceivable to watch the Red Sox deal away a reliever for the right price, even if they’re in playoff contention. Trading him could net the team a capable bench player to provide more depth for Farrell.

Capuano has shown versatility in the bullpen and brings starting experience, but he could be expendable with southpaws Andrew Miller and Craig Breslow also occupying bullpen spots.

His control has been impeccable, allowing just eight hits and two walks over those 14.1 frames. For any team in playoff contention, he would be an attractive pitcher to add.

Boston’s willingness to use starting pitching prospects as relievers also makes a deal possible. Teams will be in need of bullpen help as the non-waiver trade deadline nears at the end of July, and Capuano is more than capable of being an asset to those interested.

That need would allow Cherington to hold a higher price in return for the southpaw, especially if he continues performing at his current level. If a team is desperate enough, they'll deal a prospect with upside to make it happen.

Brock Holt

Michael Dwyer

Boston signed Ryan Roberts to take over third base while Will Middlebrooks was on the DL. After 19 at-bats and a .105/.227/.105 line, they opted to promote Brock Holt to inject some life into a struggling lineup.

He did exactly that.

Riding a hot streak in Triple-A, he did more of the same upon arriving in the big leagues, hitting .348/.429/.435 in 23 at-bats.

He was reassigned to Pawtucket on April 24 with the activation of Middlebrooks.

As the season moves into the summer, Middlebrooks’ performance at the plate could dictate whether Holt remains with the organization or is dangled as trade bait prior to the deadline.

Coming off a lackluster 2013, Middlebrooks must prove he’s ready to be the long-term answer at third base. He had a strong spring and looked good in his first few regular-season games before getting sidelined with a calf strain.

Since being activated, he’s gone 3-for-11 with one home run and three RBI.

If he continues performing well, Holt’s path to the majors looks blocked, as his two main positions are third base and second base.

Earning some more big league time as the utility infielder could help build his trade value, especially if Jonathan Herrera is preferred for that role in the long term.

It’s possible none of these players are available as the trade deadline approaches. All it takes is one winning streak to get the Red Sox back on track and performing like last year.

If they don’t, looking to deal any of the previous players could bring value back to the organization for this season and possibly into the future.

Matt's baseball opinions have been featured on MLB Trade Rumors, Yahoo! Sports, MetsBlog, Amazin' Avenue and Mets Merized Online. To keep up with Matt, you can follow him on Twitter.